BG64725B1 - Използване на производни на тетрахидропиридини (или 4-хидроксипиперидини)-бутилазоли при получаването на лекарства за лечение на болка - Google Patents
Използване на производни на тетрахидропиридини (или 4-хидроксипиперидини)-бутилазоли при получаването на лекарства за лечение на болка Download PDFInfo
- Publication number
- BG64725B1 BG64725B1 BG105141A BG10514101A BG64725B1 BG 64725 B1 BG64725 B1 BG 64725B1 BG 105141 A BG105141 A BG 105141A BG 10514101 A BG10514101 A BG 10514101A BG 64725 B1 BG64725 B1 BG 64725B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- butyl
- tetrahydropyridinyl
- phenyl
- piperidinyl
- hydroxy
- Prior art date
Links
- 208000002193 Pain Diseases 0.000 title claims abstract description 22
- 238000011282 treatment Methods 0.000 title claims abstract description 14
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 title claims abstract description 5
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 239000003814 drug Substances 0.000 title claims description 15
- 230000036407 pain Effects 0.000 title abstract description 10
- 208000001294 Nociceptive Pain Diseases 0.000 claims abstract description 12
- 208000005298 acute pain Diseases 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 241000124008 Mammalia Species 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- -1 alkoxyl radical Chemical class 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 22
- 230000000202 analgesic effect Effects 0.000 claims description 15
- 208000004296 neuralgia Diseases 0.000 claims description 12
- 208000021722 neuropathic pain Diseases 0.000 claims description 12
- 230000001154 acute effect Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 230000002981 neuropathic effect Effects 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000003254 radicals Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000001273 butane Chemical group 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 20
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- RRLIHVYOHXQZNB-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCCN1C=C(Cl)C=N1 RRLIHVYOHXQZNB-UHFFFAOYSA-N 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- MYYVNVYOLTXPDB-UHFFFAOYSA-N 1-(4-indazol-1-ylbutyl)-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3C=N2)CCC1(O)C1=CC=CC=C1 MYYVNVYOLTXPDB-UHFFFAOYSA-N 0.000 claims 1
- LBCUSCPNGDWLSX-UHFFFAOYSA-N 1-(4-indazol-2-ylbutyl)-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCCN2N=C3C=CC=CC3=C2)CCC1(O)C1=CC=CC=C1 LBCUSCPNGDWLSX-UHFFFAOYSA-N 0.000 claims 1
- QWOFETIRRVGYEC-UHFFFAOYSA-N 1-(4-indol-1-ylbutyl)-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3C=C2)CCC1(O)C1=CC=CC=C1 QWOFETIRRVGYEC-UHFFFAOYSA-N 0.000 claims 1
- TZTYVWIHVWABMX-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC(F)=CC=2)CC1 TZTYVWIHVWABMX-UHFFFAOYSA-N 0.000 claims 1
- DWLLHISUEJCRET-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-(4-methylphenyl)piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC(C)=CC=2)CC1 DWLLHISUEJCRET-UHFFFAOYSA-N 0.000 claims 1
- BPRIVJYXNGZFOZ-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=C(C=CC=2)C(F)(F)F)CC1 BPRIVJYXNGZFOZ-UHFFFAOYSA-N 0.000 claims 1
- BKPCCBJZYMDFDI-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC=CC=2)CC1 BKPCCBJZYMDFDI-UHFFFAOYSA-N 0.000 claims 1
- IQEFJLZCCQULED-UHFFFAOYSA-N 1-[4-(4,5-diphenylimidazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IQEFJLZCCQULED-UHFFFAOYSA-N 0.000 claims 1
- YAXOBPQMTRRYOS-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-(4-methoxyphenyl)piperidin-4-ol Chemical compound C1=CC(OC)=CC=C1C1(O)CCN(CCCCN2N=CC(Cl)=C2)CC1 YAXOBPQMTRRYOS-UHFFFAOYSA-N 0.000 claims 1
- ZJDHFMQZTGLTLM-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-(4-methylphenyl)piperidin-4-ol Chemical compound C1=CC(C)=CC=C1C1(O)CCN(CCCCN2N=CC(Cl)=C2)CC1 ZJDHFMQZTGLTLM-UHFFFAOYSA-N 0.000 claims 1
- RGRYAKLFIRPFCR-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=C(Cl)C=N1 RGRYAKLFIRPFCR-UHFFFAOYSA-N 0.000 claims 1
- YNPOBHOYLBLMMF-UHFFFAOYSA-N 1-[4-(benzimidazol-1-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3N=C2)CCC1(O)C1=CC=C(F)C=C1 YNPOBHOYLBLMMF-UHFFFAOYSA-N 0.000 claims 1
- PUJHXTDMPCWZES-UHFFFAOYSA-N 1-[4-(benzimidazol-1-yl)butyl]-4-(4-methylphenyl)piperidin-4-ol Chemical compound C1=CC(C)=CC=C1C1(O)CCN(CCCCN2C3=CC=CC=C3N=C2)CC1 PUJHXTDMPCWZES-UHFFFAOYSA-N 0.000 claims 1
- CQPOTRWYHMDELP-UHFFFAOYSA-N 1-[4-(benzimidazol-1-yl)butyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3N=C2)CCC1(O)C1=CC=CC=C1 CQPOTRWYHMDELP-UHFFFAOYSA-N 0.000 claims 1
- JURXEPPWCAMPQT-UHFFFAOYSA-N 1-[4-(benzotriazol-1-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3N=N2)CCC1(O)C1=CC=C(F)C=C1 JURXEPPWCAMPQT-UHFFFAOYSA-N 0.000 claims 1
- ZOLFUYXXKMOHMI-UHFFFAOYSA-N 1-[4-(benzotriazol-2-yl)butyl]-4-(4-fluorophenyl)piperidin-4-ol Chemical compound C1CN(CCCCN2N=C3C=CC=CC3=N2)CCC1(O)C1=CC=C(F)C=C1 ZOLFUYXXKMOHMI-UHFFFAOYSA-N 0.000 claims 1
- GBOMGWIDQVYPSD-UHFFFAOYSA-N 1-[4-[4-(4-chlorophenyl)pyrazol-1-yl]butyl]-4-phenylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN(N=C1)C=C1C1=CC=C(Cl)C=C1 GBOMGWIDQVYPSD-UHFFFAOYSA-N 0.000 claims 1
- HSFXDMSGPROVRE-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperidin-4-ol Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCC(O)(C=2C=CC(Cl)=CC=2)CC1 HSFXDMSGPROVRE-UHFFFAOYSA-N 0.000 claims 1
- NCSUPLXPBOEGCC-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(triazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCCN1C=CN=N1 NCSUPLXPBOEGCC-UHFFFAOYSA-N 0.000 claims 1
- ABKAYOFKLFOUTI-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-(4-indazol-1-ylbutyl)piperidin-4-ol Chemical compound C1CN(CCCCN2C3=CC=CC=C3C=N2)CCC1(O)C1=CC=C(F)C=C1 ABKAYOFKLFOUTI-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- QPDUNGVMKHTKOD-UHFFFAOYSA-N 4-phenyl-1-(4-pyrazol-1-ylbutyl)piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=CC=N1 QPDUNGVMKHTKOD-UHFFFAOYSA-N 0.000 claims 1
- JFHHUMHVYLZACW-UHFFFAOYSA-N 4-phenyl-1-[4-(1,2,4-triazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=NC=N1 JFHHUMHVYLZACW-UHFFFAOYSA-N 0.000 claims 1
- CDQRJAXVBKJQLT-UHFFFAOYSA-N 4-phenyl-1-[4-(2-phenylimidazol-1-yl)butyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CCCCN1C=CN=C1C1=CC=CC=C1 CDQRJAXVBKJQLT-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241000282414 Homo sapiens Species 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229940035676 analgesics Drugs 0.000 description 9
- 239000000730 antalgic agent Substances 0.000 description 9
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 7
- 229960005181 morphine Drugs 0.000 description 6
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 6
- 229960005301 pentazocine Drugs 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 229940120889 dipyrone Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- DJGAAPFSPWAYTJ-UHFFFAOYSA-M metamizole sodium Chemical compound [Na+].O=C1C(N(CS([O-])(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 DJGAAPFSPWAYTJ-UHFFFAOYSA-M 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 125000006519 CCH3 Chemical group 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000581650 Ivesia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 208000008035 Back Pain Diseases 0.000 description 1
- 101100234822 Caenorhabditis elegans ltd-1 gene Proteins 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- 208000004983 Phantom Limb Diseases 0.000 description 1
- 206010056238 Phantom pain Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009801467A ES2151828B1 (es) | 1998-07-10 | 1998-07-10 | Empleo de derivados de tetrahidropiridinas (ohidroxi-piperidinas)-b utilazoles en la elaboracion de un medicamento para el tratamiento del dolor. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG105141A BG105141A (en) | 2001-10-31 |
| BG64725B1 true BG64725B1 (bg) | 2006-01-31 |
Family
ID=8304473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG105141A BG64725B1 (bg) | 1998-07-10 | 2001-01-10 | Използване на производни на тетрахидропиридини (или 4-хидроксипиперидини)-бутилазоли при получаването на лекарства за лечение на болка |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6384055B1 (cs) |
| EP (1) | EP1097698B1 (cs) |
| JP (1) | JP2002520261A (cs) |
| KR (1) | KR100758740B1 (cs) |
| CN (1) | CN1134259C (cs) |
| AR (1) | AR019894A1 (cs) |
| AT (1) | ATE239476T1 (cs) |
| AU (1) | AU747073C (cs) |
| BG (1) | BG64725B1 (cs) |
| BR (1) | BR9912000A (cs) |
| CA (1) | CA2336784A1 (cs) |
| CO (1) | CO5060468A1 (cs) |
| CZ (1) | CZ292015B6 (cs) |
| DE (1) | DE69907685T2 (cs) |
| DK (1) | DK1097698T3 (cs) |
| ES (2) | ES2151828B1 (cs) |
| HU (1) | HUP0102868A3 (cs) |
| ID (1) | ID28817A (cs) |
| IL (1) | IL140854A (cs) |
| MX (1) | MXPA01000369A (cs) |
| NO (1) | NO20010147D0 (cs) |
| NZ (1) | NZ509556A (cs) |
| PL (1) | PL194721B1 (cs) |
| PT (1) | PT1097698E (cs) |
| RU (1) | RU2202347C2 (cs) |
| SK (1) | SK372001A3 (cs) |
| TR (1) | TR200100043T2 (cs) |
| TW (1) | TW589317B (cs) |
| UA (1) | UA57149C2 (cs) |
| WO (1) | WO2000002519A2 (cs) |
| ZA (1) | ZA200100240B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6995144B2 (en) * | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| EP1481680A1 (en) * | 2003-05-30 | 2004-12-01 | Aventis Pharma Deutschland GmbH | Use of S1P |
| EP1648879B1 (en) * | 2003-07-24 | 2008-10-22 | Euro-Celtique S.A. | Heteroaryl-tetrahydropyridyl compounds useful for treating or preventing pain |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996004287A1 (fr) * | 1994-07-29 | 1996-02-15 | Laboratorios Del Dr. Esteve, S.A. | Tetrahydropyridine-(ou 4-hydroxypiperidine) alkylazoles ayant une activite pour les recepteurs sigma et/ou 5ht1a |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1833618A3 (ru) * | 1991-01-28 | 1995-07-09 | Институт химических наук АН Республики Казахстан | 1-(3-бутоксипропил)-4-оксопиперидин в качестве промежуточного соединения в синтезе гидрохлорида 1-(3-бутоксипропил)-4-фенил-4-пропионилоксипиперидина, обладающего анальгетической активностью |
| JPH084287A (ja) * | 1994-06-16 | 1996-01-09 | Tateyama Alum Ind Co Ltd | 柱体のコンクリート床面立設方法及びこれに用いる治具 |
| EP0906104A4 (en) * | 1996-03-25 | 2003-12-10 | Lilly Co Eli | PAIN TREATMENT PROCESS |
-
1998
- 1998-07-10 ES ES009801467A patent/ES2151828B1/es not_active Expired - Fee Related
-
1999
- 1999-07-01 CO CO99041288A patent/CO5060468A1/es unknown
- 1999-07-07 AR ARP990103289A patent/AR019894A1/es unknown
- 1999-07-09 EP EP99929333A patent/EP1097698B1/en not_active Expired - Lifetime
- 1999-07-09 CZ CZ200175A patent/CZ292015B6/cs not_active IP Right Cessation
- 1999-07-09 US US09/743,085 patent/US6384055B1/en not_active Ceased
- 1999-07-09 AT AT99929333T patent/ATE239476T1/de not_active IP Right Cessation
- 1999-07-09 PT PT99929333T patent/PT1097698E/pt unknown
- 1999-07-09 PL PL99345781A patent/PL194721B1/pl not_active IP Right Cessation
- 1999-07-09 IL IL140854A patent/IL140854A/en not_active IP Right Cessation
- 1999-07-09 WO PCT/ES1999/000222 patent/WO2000002519A2/es not_active Ceased
- 1999-07-09 TR TR2001/00043T patent/TR200100043T2/xx unknown
- 1999-07-09 US US10/355,216 patent/USRE39113E1/en not_active Expired - Fee Related
- 1999-07-09 AU AU46171/99A patent/AU747073C/en not_active Ceased
- 1999-07-09 MX MXPA01000369A patent/MXPA01000369A/es active IP Right Grant
- 1999-07-09 SK SK37-2001A patent/SK372001A3/sk unknown
- 1999-07-09 CA CA002336784A patent/CA2336784A1/en not_active Abandoned
- 1999-07-09 ID IDW20010066A patent/ID28817A/id unknown
- 1999-07-09 CN CNB998102083A patent/CN1134259C/zh not_active Expired - Fee Related
- 1999-07-09 DK DK99929333T patent/DK1097698T3/da active
- 1999-07-09 JP JP2000558783A patent/JP2002520261A/ja not_active Ceased
- 1999-07-09 BR BR9912000-3A patent/BR9912000A/pt not_active Application Discontinuation
- 1999-07-09 DE DE69907685T patent/DE69907685T2/de not_active Expired - Lifetime
- 1999-07-09 HU HU0102868A patent/HUP0102868A3/hu unknown
- 1999-07-09 ES ES99929333T patent/ES2198136T3/es not_active Expired - Lifetime
- 1999-07-09 NZ NZ509556A patent/NZ509556A/xx unknown
- 1999-07-09 RU RU2001103738/14A patent/RU2202347C2/ru not_active IP Right Cessation
- 1999-07-09 KR KR1020017000391A patent/KR100758740B1/ko not_active Expired - Fee Related
- 1999-08-10 TW TW088112508A patent/TW589317B/zh not_active IP Right Cessation
- 1999-09-07 UA UA2001010210A patent/UA57149C2/uk unknown
-
2001
- 2001-01-09 NO NO20010147A patent/NO20010147D0/no not_active Application Discontinuation
- 2001-01-09 ZA ZA200100240A patent/ZA200100240B/en unknown
- 2001-01-10 BG BG105141A patent/BG64725B1/bg unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996004287A1 (fr) * | 1994-07-29 | 1996-02-15 | Laboratorios Del Dr. Esteve, S.A. | Tetrahydropyridine-(ou 4-hydroxypiperidine) alkylazoles ayant une activite pour les recepteurs sigma et/ou 5ht1a |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0869792B1 (en) | 4-substituted piperidine analogs and their use as subtype selective nmda receptor antagonists | |
| US6245773B1 (en) | 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines | |
| DK2531191T3 (en) | Sigma ligands for use in the prevention and / or treatment of post-operative pain | |
| US20230339913A1 (en) | Substituted pyridine derivatives as sarm1 inhibitors | |
| JP2000502352A (ja) | ４位置換ピペリジン類似体及びサブタイプ選択的ｎｍｄａレセプターアンタゴニストとしてのその使用 | |
| KR101855357B1 (ko) | 오피오이드 유도성 통각과민에서의 시그마 리간드의 용도 | |
| EA005934B1 (ru) | Замещённые анилиновые пиперидины в качестве селективных антагонистов мсн | |
| SG190745A1 (en) | Use of sigma ligands in bone cancer pain | |
| MXPA05009290A (es) | Derivados heterociclicos que contienen nitrogeno que tienen estirilo 2,6-disustituido. | |
| BG64725B1 (bg) | Използване на производни на тетрахидропиридини (или 4-хидроксипиперидини)-бутилазоли при получаването на лекарства за лечение на болка | |
| EP2256114B1 (en) | Amide derivative and pharmaceutical composition containing the same | |
| JP6313264B2 (ja) | ケイ皮酸アミド誘導体を含有する医薬 | |
| WO2021252709A1 (en) | Compounds, compositions, and methods for treating, ameliorating, and/or preventing sigma receptor related diseases and/or disorders | |
| EP0291244A1 (en) | Cyclic carbamate derivatives |